Rhodol triflate | 1189743-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: Rhodol triflate
• 英文别名: [6'-(Methoxymethoxy)-3-oxospiro[2-benzofuran-1,9'-xanthene]-3'-yl] trifluoromethanesulfonate
• CAS: 1189743-04-1
• 化学式: C₂₃H₁₅F₃O₈S
• 分子量: 508.429
• InChiKey: QGWJBJYKLIGRJE-UHFFFAOYSA-N

物化性质

• 沸点：
  628.7±55.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Rhodol triflate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 22.5h， 生成 N-methylrhodol
  参考文献：
  名称：

  HKGreen-4 在活细胞和组织中对过氧亚硝酸盐的分子成像

  摘要：

  过氧亚硝酸盐 (ONOO(-)) 是一氧化氮和超氧化物的自由基结合反应的产物，是一种有效的生物氧化剂，涉及广泛的生理和病理过程。在此，我们报告了一种用于过氧亚硝酸盐检测和成像的新型荧光探针 HKGreen-4 的开发、表征和生物学应用。HKGreen-4 利用过氧亚硝酸盐触发的氧化 N-脱芳基化反应来实现对化学系统和生物样品中过氧亚硝酸盐的异常灵敏和选择性的荧光开启响应。我们已经彻底评估了 HKGreen-4 在细胞内过氧亚硝酸盐成像方面的效用，更重要的是，证明 HKGreen-4 可以有效地用于可视化在大肠杆菌攻击的巨噬细胞和动脉粥样硬化小鼠模型的活组织中产生的内源性过氧亚硝酸盐。该探针应作为一种强大的分子成像工具，在各种生理和病理背景下探索过氧亚硝酸盐生物学。

  DOI：

  10.1021/ja504624q
• 作为产物：
  描述：

  荧光素 在 吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Rhodol triflate
  参考文献：
  名称：

  A Reductant-Resistant and Metal-Free Fluorescent Probe for Nitroxyl Applicable to Living Cells

  摘要：

  Nitroxyl (HNO) is a one-electron reduced and protonated derivative of nitric oxide (NO) and has characteristic biological and pharmacological effects distinct from those of NO. However, studies of its biosynthesis and activities are restricted by the lack of versatile FIN detection methods applicable to living cells. Here, we report the first metal-free and reductant-resistant HNO imaging probe available for use in living cells, P-Rhod. It consists of a rhodol derivative moiety as the fluorophore, linked via an ester moiety to a diphenylphosphinobenzoyl group, which forms an aza-ylide upon reaction with HNO. Intramolecular attack of the aza-ylide on the ester carbonyl group releases a fluorescent rhodol derivative. P-Rhod showed high selectivity for HNO in the presence of various biologically relevant reductants, such as glutathione and ascorbate, in comparison with previous HNO probes. We show that P-Rhod can detect not only HNO enzymatically generated in the horseradish peroxidase-hydroxylamine system in vitro but also intracellular HNO release from Angeli's salt in living cells. These results suggest that P-Rhod is suitable for detection of HNO in living cells.

  DOI：

  10.1021/ja404757s

文献信息

• [EN] FLUOROPHORE COMPOUNDS<br/>[FR] COMPOSÉS FLUOROPHORES
  申请人：VERSITECH LTD

  公开号：WO2009121244A1

  公开（公告）日：2009-10-08

  Provided herein are fluorophore compounds including rhodol and rhodamine compounds which can be used as fluorescent labels and/or fluorogenic probes and methods of making same. Provided also herein are methods that can be used to track, measure, detect, or screen biological species such as protein, DNA, enzyme, antibody, organelle, cell, tissue, drug, hormone, nucleotide, nucleic acid, polysaccharide or lipid in living organisms. Specifically, the methods include the steps of contacting any of the fluorophore compounds, rhodol compounds and rhodamine compounds disclosed herein with the biological species to form one or more fluorescent compounds, and measuring fluorescence properties of the fluorescent compounds. Provided also herein are high-throughput screening fluorescent methods for detecting or screening biological species.

  本文提供了包括罗多尔和罗丹明化合物在内的荧光物质，可用作荧光标记剂和/或荧光探针，并提供了制备这些化合物的方法。本文还提供了可用于跟踪、测量、检测或筛选蛋白质、DNA、酶、抗体、细胞器、细胞、组织、药物、激素、核苷酸、核酸、多糖或脂质等生物种类在活体中的方法。具体而言，这些方法包括将本文披露的任何荧光物质、罗多尔化合物和罗丹明化合物与生物种类接触以形成一个或多个荧光化合物，并测量荧光化合物的荧光特性。本文还提供了用于检测或筛选生物种类的高通量筛选荧光方法。
• [EN] LUMINESCENCE QUENCHERS AND FLUOROGENIC PROBES FOR DETECTION OF REACTIVE SPECIES<br/>[FR] EXTINCTEURS DE LUMINESCENCE ET SONDES FLUOROGÉNIQUES DESTINÉS À LA DÉTECTION D'UNE ESPÈCE RÉACTIVE
  申请人：VERSITECH LTD

  公开号：WO2009121247A1

  公开（公告）日：2009-10-08

  Provided herein are compounds or fluorogenic probes which can be used as reagents for measuring, detecting and/or screening ROS or RNS such as peroxynitrite or hypochlorite. Provided also herein are methods that can be used to measure, directly or indirectly, the amount of peroxynitrite or hypochlorite in chemical samples and biological samples such as cells and tissues in living organisms. Specifically, the methods include the steps of contacting the fluorogenic probes disclosed herein with the samples to form one or more fluorescent compounds, and measuring fluorescence properties of the fluorescent compounds. Provided also herein are high-throughput screening fluorescent methods for detecting or screening peroxynitrite or compounds that can increase or decrease the level of peroxynitrite or hypochlorite in chemical and biological samples.

  本发明提供了可用于测量、检测和/或筛选过氧亚硝酸盐或次氯酸盐等活性氧或活性氮化合物的化合物或荧光生成探针。本发明还提供了可用于直接或间接测量化学样品和生物样品（如活体生物的细胞和组织）中过氧亚硝酸盐或次氯酸盐含量的方法。具体而言，这些方法包括将本发明披露的荧光生成探针与样品接触以形成一种或多种荧光化合物，并测量荧光化合物的荧光特性。本发明还提供了用于检测或筛选过氧亚硝酸盐或能够增加或减少化学和生物样品中过氧亚硝酸盐或次氯酸盐水平的化合物的高通量筛选荧光方法。
• A Bioorthogonal Reaction of <i>N</i> ‐Oxide and Boron Reagents
  作者：Justin Kim、Carolyn R. Bertozzi

  DOI：10.1002/anie.201508861

  日期：2015.12.21

  The development of bioorthogonal reactions has classically focused on bond‐forming ligation reactions. In this report, we seek to expand the functional repertoire of such transformations by introducing a new bond‐cleaving reaction between N‐oxide and boron reagents. The reaction features a large dynamic range of reactivity, showcasing second‐order rate constants as high as 2.3×103 M−1 s−1 using diboron

  生物正交反应的发展经典地集中在成键连接反应上。在本报告中，我们试图通过在N-氧化物和硼试剂之间引入新的键断裂反应来扩展此类转化的功能库。该反应具有较大的动态反应性范围，使用二硼反应伙伴的二级速率常数高达 2.3×10 3  M -1  s -1 。Diboron 试剂在毫摩尔浓度下表现出最小的细胞毒性，可穿透细胞膜并有效降低N-哺乳动物细胞内的氧化物。因此，这种基于微小成分的新生物正交过程非常适合在化学控制下激活细胞内的分子。此外，我们证明了自然界的代谢多样性使得能够使用天然存在的官能团，这些官能团与非生物成分一起表现出固有的生物相容性，用于特定生物体的应用。
• [EN] BIOORTHOGONAL REACTION OF AN AMINE N-OXIDE AND A BORON AGENT<br/>[FR] RÉACTION BIO-ORTHOGONALE D'UN N-OXYDE D'AMINE ET D'UN AGENT CONTENANT DU BORE
  申请人：UNIV CALIFORNIA

  公开号：WO2017027337A1

  公开（公告）日：2017-02-16

  Methods for chemoselective modification of a target molecule comprising an amine N-oxide in a biological sample are provided. Aspects of the methods include selectively reacting the amine N-oxide group of the target molecule with a boron agent, where the reacting reduces the amine N-oxide to an amine to produce a modified target molecule. Modification of the target molecule using the subject methods may produce an activated target molecule, e.g., a detectable or bioactive. In some cases, chemoselective modification leads to cleavage of the modified target molecule to produce a first target fragment and a second target fragment. Also provided are compositions useful in practicing various embodiments of the subject methods.

  提供了一种在生物样本中对含有胺N-氧化物的目标分子进行化学选择性修饰的方法。该方法的方面包括选择性地将目标分子的胺N-氧化物基团与硼试剂发生反应，其中该反应将胺N-氧化物还原为胺，从而产生修饰后的目标分子。使用这些方法对目标分子进行修饰可能产生一个活化的目标分子，例如，一个可检测或生物活性的分子。在某些情况下，化学选择性修饰会导致修饰后的目标分子发生裂解，产生第一目标片段和第二目标片段。还提供了在实践主题方法的各种实施方案中有用的组合物。
• Construction of a Library of Rhodol Fluorophores for Developing New Fluorescent Probes
  作者：Tao Peng、Dan Yang

  DOI：10.1021/ol902706b

  日期：2010.2.5

  A highly efficient and concise synthetic scheme for rhodol fluorophores is developed with palladium-catalyzed amination reaction as the key step. This new synthetic route is utilized to construct a rhodol library, potentially useful for the design of novel fluorescent probes.

  以钯催化的胺化反应为关键步骤，开发了一种高效，简洁的合成铑荧光团的合成方案。该新的合成途径用于构建可用于设计新型荧光探针的rhodol文库。